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Caribbean Island hopping - tips & ideas?

We are 4 people in our mid 20s and we want to explore as much as we can from the Caribbean islands. Time frame 20Dec - 5th January, budget about 2000 Euros per person, starting from europe.

Do you have any suggestions for a good route and easy transport between the islands? What is the best place to start the trip.? We were thinking of starting from Cuba and then visiting Haiti and the Dominican Republic.... But from what i saw from Cuba it works only with flights, i didn't find much about ferry connections from and to cuba (Which makes it more expensive).

So any ideas and tips about possible starting point and routes are super welcome.

I agree with Blamona. With your budget this will not happen during the time frame you chose. The better time frames would be the first 2 weeks of November or December before high season starts.

You can look at Tiara and Insel air web-sites to see the logistics of going to other Islands by air.

We have flown from Aruba to Curacao.

We've been looking a day trips from Barbados to Grenada and St. Vincent, but it was $600 per person each destination.

When we went to St. Lucia they had day trips to St. Vincent for $500 per couple. There is a boat trip to Martinque for about 1/2 that.

From St. Thomas you can take the ferry to St. John. There are day trips to the British Virgin Islands.

Were you planning to actually stay on another Island for an extended period of time? Doing so will cost so much extra time and money for air and hotels. Again, with that budget it won't happen. Day trips are more cost effective.

Travelling to the Caribbean from Europe does not require overnights in MIA or changing planes in SJU. You have direct flight options to pretty much all of the major islands from London, Paris, Amsterdam and Madrid plus Mexico. BA & VS cover Cuba/Cancun/Barbados/Jamaica/Antigua/St Lucia/Grenada/St Kitts/St Lucia, AF from Paris takes to you Martinique Guadeloupe St Martin from which you can take a ferry to Anguilla in 15 mins and a catamaran to St Barths, KL from AMS for the Dutch Antilles. Flying from Madrid will take you to several Latin American destinations. There are several charters from other European cities.

Express des iles operate a scheduled catamaran service between Martinique Guadeloupe and Dominica St Lucia and some smaller islands. Journey time is about 4 hours on open water from Martinique to Guadeloupe, costs about $100 return.http://www.express-des-iles.com/index.cfm?lng=en

Having said all this, on a EUR2000 budget over Christmas will be difficult if not impossible, even on islands that offer inexpensive lodgings with no minimum stays. Check out this airline for low cost flights from France http://www.xl.com/en/

But, once you get to a Caribbean Island in order to get to another Caribbean Island it may require going to Miami or Puerto Rico to get there. Islands that don't have another access route like a ferry or puddle jumper plane and must use a commercial airline to get to usually requires flying back to the US or to PR to get to it.

For example, if you land in Jamaica and want to go to Nassau Bahamas, you will first have to fly to Miami and change flights.

Hopping around the Caribbean is not as easy as some people think and can get very costly.

Tiara Air and Insel Air have options for hopping around some of the Caribbean, but their flights and destinations are limited.

As others have said you are looking to travel at the most expensive time of the year with many places having week or longer minimums.

The island groupings that I'm familiar with that have easy ferry connections are:

St. Martin/Anguilla/St. Barts.
St. Martin has a range of accommodations in all price ranges with tons of dining opportunities. You may be able to find accommodation here that meets your budget. You'll have to look hard to find less expensive accommodations on Anguilla. Some do exist but they are small properties and likely already booked. Don't even bother looking on St. Barts. Accommodations over Christmas will likely be your entire budget for one night.

The U.S. and British Virgin Islands.
There are ferries that ply the waters throughout the Virgin Islands. You can reach Virgin Gorda, St. John and Tortola via ferry from St. Thomas. Ferries run from Tortola to Anagada and Jost Van Dyke. There may be other ferry routes also. Tortola has some lower cost accommodations. Look at the offerings at Cane Garden Bay. That also happens to be a stunning beach. You may be able to find a villa to accommodate your party on some of these islands. That way you'll also have kitchen facilities which can save you some money on food costs. My brother just rented a villa for next spring on Virgin Gorda on VRBO. He got a really great price that even includes a car.

St. Kitts and Nevis.
Again, you may find accommodations (villa?) on St. Kitts that will fit your budget. Nevis, probably not.

Also check some of the islands in the Grenadines. There may be ferry service but I'm not sure.

A post-script: I think Haiti is still pretty much a mess from the 2010 earthquake although there may be a couple of resort areas that weren't damaged.

Agree with Sharona,pertaining to Haiti. If fact I would skip Dominican Republic although it is more then likely less costly.

If possible on your budget if seeing more than one island is what you want I would go to St. Martin. There is the dutch side/French side. From Marigot you can take a ferry for day trips to Anguilla and also St. Barts. That time frame you better start planning for as all ready stated it is the high season in the Caribbean.

I came across this interesting thread looking for information on island hopping in the Caribbean sea. I'm planning to travel from St. Lucia to Guadeloupe via Martinique and Dominica using the inter-island ferry service.

However, every island seems to require a return ticket or an onward ticket upon arrival to pass immigration (at least according to Lonely Planet). Does this mean that I would need to buy all trips in advance (is this even possible) or does it suffice if I show them the long-haul flight ticket back home (Europe in my case) at the end of my planned trip.

You probably won't even be asked to show your "onward ticket" but if you are, your return ticket "back home" will suffice. Local authorities just want to be sure you'll be "moving on" and not trying to stay indefinitely on their particular island.

I would not rely on guidebooks for immigration info since they can be out of date, check each country's website. I have never been asked to prove that I have an onward or return ticket for any visit I have made to a Caribbean island, generally immigration just ask how long I intend to stay and sometimes ask where I am staying.